Hydrochloric Acid → HCID 54597085, compound

HRID 1853143Notes

Reaction equation

HRID 1853143 reaction equation
Cl.O1CCOCC1.C(OC(=O)[N:14]([C:22]1[C:27]([C:28]2[O:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:31][N:32]=2)=[N:26][C:25]([C:39]#[C:40][CH2:41][OH:42])=[CH:24][N:23]=1)C(OC(C)(C)C)=O)(C)(C)C>CO>[NH2:14][C:22]1[N:23]=[CH:24][C:25]([C:39]#[C:40][CH2:41][OH:42])=[N:26][C:27]=1[C:28]1[O:29][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:31][N:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66724849HCID 66724849, compound

Product 1

HCID 54597085HCID 54597085, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4M HCl in dioxane (101.3 μL, 0.405 mmol) was added to a stirred solution of tert-butyl(5-(3-hydroxyprop-1-yn-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)(tert-butoxycarbonyl)carbamate (40 mg, 0.08105 mmol) in MeOH (1 mL) and the reaction allowed to stir at ambient temperature for 20 hours then concentrated in vacuo. The residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound as an yellow solid (22.4 mg, 94% Yield). MS (ES+) 294.2.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  3. customThe fractions were collected
  4. customfreeze-dried

Sources & evidence

ORD record
ord-1b4b959787ae4d6d96e28cf586326712
Source dataset
uspto-grants-2015_02
Patent number
US08962631B2

Reaction notes

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